Global Patent Index - EP 1003717 A1

EP 1003717 A1 2000-05-31 - PREPARATION AND USES OF HYDROCARBYLNITRONES

Title (en)

PREPARATION AND USES OF HYDROCARBYLNITRONES

Title (de)

VERFAHREN UND VERWENDUNG VON HYDROCARBYLNITRONEN

Title (fr)

PREPARATION ET UTILISATIONS D'HYDROCARBYLNITRONES

Publication

EP 1003717 A1 (EN)

Application

EP 98938289 A

Priority

  • US 9816110 W
  • US 90552597 A

Abstract (en)

[origin: WO9906362A1] Nitrones are produced by reaction of primary amine with aldehyde or ketone, in the presence of a transition metal-containing oxidation catalyst, and a peroxidic compound. The nitrone can then be reacted with a vinylaromatic compound to produce a 2-hydrocarbyl-5-arylisoxazolidine. Both such reactions can be conducted concurrently by including the vinylaromatic compound in the initial reaction mixture. Hydrogenation of the 2-hydrocarbyl-5-arylisoxazolidine, e.g., using hydrogen and a palladium-carbon catalyst, forms an N-hydrocarbyl-3-aryl-3-hydroxypropylamine. Such reactions enable, inter alia, synthesis of the racemic hydrochloride salt of N-methyl-3-phenyl-3-[4-trifluoromethyl]-propylamine, known generically as fluoxetine hydrochloride, a widely used antidepressant.

IPC 1-7 (main, further and additional classification)

C07C 291/02; C07C 217/26

IPC 8 full level (invention and additional information)

C07C 217/26 (2006.01); C07C 291/02 (2006.01)

CPC (invention and additional information)

C07C 291/02 (2013.01); C07C 217/26 (2013.01)

Citation (search report)

See references of WO 9906362A1

Designated contracting state (EPC)

BE CH DE ES FR GB IT LI NL

EPO simple patent family

WO 9906362 A1 19990211; EP 1003717 A1 20000531; US 5998627 A 19991207

INPADOC legal status


2002-04-10 [18D] DEEMED TO BE WITHDRAWN

- Effective date: 20010925

2001-06-27 [17Q] FIRST EXAMINATION REPORT

- Effective date: 20010514

2000-05-31 [17P] REQUEST FOR EXAMINATION FILED

- Effective date: 20000225

2000-05-31 [AK] DESIGNATED CONTRACTING STATES:

- Kind Code of Ref Document: A1

- Designated State(s): BE CH DE ES FR GB IT LI NL